64292-70-2Relevant academic research and scientific papers
Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate
Shabalin, Dmitrii A.,Dvorko, Marina Yu.,Schmidt, Elena Yu.,Trofimov, Boris A.
supporting information, p. 2703 - 2715 (2021/04/07)
A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridinesvia t-BuOK/DMSO-promotedC-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of thein situgenerated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available starting materials and the absence of transition-metal catalysts, oxidants and undesirable byproducts. A wide synthetic utility of the developed approach was demonstrated by the synthesis of trisubstituted, tetrasubstituted and fused pyridines.
Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
Kontokosta, Dimitra,Mueller, Daniel S.,Mo, Dong-Liang,Pace, Wiktoria H.,Simpson, Rachel A.,Anderson, Laura L.
, p. 2097 - 2104 (2016/04/01)
A Chan-Lam reaction has been used to prepare N-alkenyl-α,β-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. I
Pyrylium Compounds. 30. C-Alkylation of 1,3,5-Triaryl-pentene-1,5-dione Enolates: A Simple Approach to 3-Alkylsubstituted 2,4,6-Triarylpyrylium Salts
Fischer, Gerhard W.
, p. 983 - 997 (2007/10/02)
1,3,5-Triaryl-pentene-1,5-dione enolates (10), obtainable in crystalline form from 2,4,6-triarylpyrylium pseudobases (9) and sodium methoxide in benzene/ether, react in dipolar aprotonic solvents (e.g.DMSO, DMF) with various types of alkyl iodides to give
Boron Trifluoride as a Cyclodehydrating Agent: Synthesis of Nitrogen Heterocycles via Pyrylium Tetrafluoroborates
Elshafie, Sayed M. M.
, p. 427 - 428 (2007/10/02)
Pyrylium cations (1-12,Z = O+) have been prepared in high yields by the interaction of chalkones (in slight excess) and different ketones using BF3-etherate as cyclodehydrating agent or from 1,5-diketones in the presence of HBr and chalkone as hydrogen abstractor.The pyrylium cations have been converted into the corresponding nitrogen heterocycles (1-12;Z=N).
Kinetics and Mechanisms of Nucleophilic Displacements with Heterocycles as Leaving Groups. 2. N-Benzylpyridinium Cations: Rate Variation with Steric Effects in the Leaving Group
Katritzky, Alan R.,El-Mowafy, Azzahra M.,Musumarra, Giuseppe,Sakizadeh, Kumars,Sana-Ullah, Choudhry,et al.
, p. 3823 - 3830 (2007/10/02)
N-Benzyl groups are transferred to piperidine from pyridinium ions by unimolecular SN1 and/or bimolecular SN2 mechanisms.Steric acceleration by α-phenyl groups is reduced by an adjacent β-methyl group but increased by constraining th
